Methyl iodide → 5-fluoro-6-iodo-1-methyl-1H-indole

HRID 222468Notes

Reaction equation

HRID 222468 reaction equation
[I:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][C:3]=1[F:11].[H-].[Na+].I[CH3:15]>CN(C=O)C>[F:11][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:2]=1[I:1])[N:8]([CH3:15])[CH:7]=[CH:6]2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 226127725-fluoro-6-iodo-1H-indole

Product 1

HCID 685242905-fluoro-6-iodo-1-methyl-1H-indoleYield 96.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 6-iodo-5-fluoro-1H-indole (0.495 g, 1.890 mmol) in dry DMF (7.0 mL) was added sodium hydride (55% suspension in oil) (0.124 g, 2.840 mmol) at 0° C. The mixture was stirred at 0° C. for 30 min, and then iodomethane (0.15 mL, 2.47 mmol) was added. The mixture was stirred for 1 hour at room temperature, and then quenched with ice and extracted with EtOAc (50 mL). The organic layer was washed with water, brine, dried over MgSO4, filtered, and concentrated. The residue was purified by column chromatography (EtOAc-hexane, 1:9) to afford 5-fluoro-6-iodo-1-methyl-1H-indole as a colorless solid (0.50 g, 96%).

Workup

  1. stirringThe mixture was stirred for 1 hour at room temperature
  2. customquenched with ice
  3. extractionextracted with EtOAc (50 mL)
  4. washThe organic layer was washed with water, brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography (EtOAc-hexane, 1:9)

Sources & evidence

ORD record
ord-a508b61691fa4a808cabed1c880ca87c
Source dataset
uspto-grants-2012_06
Patent number
US08207216B2

Reaction notes

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